1-(1-(1-oxa-2-butenyl))-2-methoxy-4-nitrobenzene | 153001-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1-(1-oxa-2-butenyl))-2-methoxy-4-nitrobenzene
• 英文别名: 1-But-2-enoxy-2-methoxy-4-nitrobenzene
• CAS: 153001-63-9
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: CUKQCGUERDQUIC-UHFFFAOYSA-N

物化性质

• 沸点：
  354.5±27.0 °C(predicted)
• 密度：
  1.160±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1-(1-oxa-2-butenyl))-2-methoxy-4-nitrobenzene 在 platinum(IV) oxide 盐酸 、 四氯化碳 、 sodium hydroxide 、 palladium on activated charcoal 、 N-溴代丁二酰亚胺(NBS) 、 PPA 、 二甲基硫 、 偶氮二异丁腈 、 硫酸 、 氢气 、 双氧水 、 三正丁基氢锡 、 甲酸铵 、 吡啶盐酸盐 、 sodium hydride 、 臭氧 、 三苯基膦 、 (-)-Monoisopinocampheylborane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， -78.0~180.0 ℃ 、137.9 kPa 条件下， 反应 40.91h， 生成 (S)-8-Chloromethyl-1-methyl-7,8-dihydro-6H-furo[3,2-e]indol-4-ol
  参考文献：
  名称：

  Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: an asymmetric hydroboration mediated synthesis of the alkylation subunits

  摘要：

  1,2-Dihydro-1-(chloromethyl)-5-hydroxy-8-methyl-3H-furano[3,2-e] indole (CFI) as a novel re; placement of the cyclopropylpyrroloindoline (CPI) alkylation subunit of CC-1065, U-71184, and U-73975 (adozelesin) has been synthesized and incorporated into a series of efficacious antineopIastic agents. A partial solution to an asymmetric synthesis of the CFI alkylation subunit has been achieved by the implementation of an asymmetric hydroboration reaction of an intermediate 3-methyleneindoline (13). Extension to the asymmetric synthesis of the CBI and CI alkylation subunits is presented. The demonstration and comparative study of the sequence-selective DNA alkylation properties of the CFI-based agents are detailed, and the preliminary in vitro and in vivo antineoplastic propertes of these agents in the human epidermoid cell lung carcinoma (T222) are described.

  DOI：

  10.1021/jm00028a005
• 作为产物：
  描述：

  1-溴-2-丁烯 、 potassium 2-methoxy-4-nitrophenolate 在 potassium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以91%的产率得到1-(1-(1-oxa-2-butenyl))-2-methoxy-4-nitrobenzene
  参考文献：
  名称：

  Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: an asymmetric hydroboration mediated synthesis of the alkylation subunits

  摘要：

  1,2-Dihydro-1-(chloromethyl)-5-hydroxy-8-methyl-3H-furano[3,2-e] indole (CFI) as a novel re; placement of the cyclopropylpyrroloindoline (CPI) alkylation subunit of CC-1065, U-71184, and U-73975 (adozelesin) has been synthesized and incorporated into a series of efficacious antineopIastic agents. A partial solution to an asymmetric synthesis of the CFI alkylation subunit has been achieved by the implementation of an asymmetric hydroboration reaction of an intermediate 3-methyleneindoline (13). Extension to the asymmetric synthesis of the CBI and CI alkylation subunits is presented. The demonstration and comparative study of the sequence-selective DNA alkylation properties of the CFI-based agents are detailed, and the preliminary in vitro and in vivo antineoplastic propertes of these agents in the human epidermoid cell lung carcinoma (T222) are described.

  DOI：

  10.1021/jm00028a005